Patent GB-744831-A (GB)
Title: Improvements in or relating to polyesters
Inventor: AITKEN ROXBURGH RICHMOND
IPC: C07D303/42
Filed: 1953-01-30
Abstract: The invention comprises epoxidized linear polyesters of saturated aliphatic or aromatic dihydric alcohols, dicarboxylic acids free from non-benzenoid unsaturation and unsaturated fatty acids derived from naturally occurring triglyceride oils, which latter may be used in conjunction with saturated fatty acids or aromatic monocarboxylic acids.  Unsaturated polyesters are prepared from the acids and dihydric alcohols by conventional methods.  They may be epoxidized by known methods such as oxidation using a peracid, e.g. perbenzoic, perphthalic or peracetic acid or by dehydrohalogenation with alkali of the halohydrin obtained from the unsaturated polyesters with hypohalous acid.  The degree of epoxidation may be varied by variation of the time of contact of the polyester with the peracid or the halohydrin with alkali or by variation of the quantity of per acid or hypohalous acid used.  According to examples, adipic acid and propylene glycol are heated with oleic acid, lauric acid and tobacco seed oil acids, linseed oil acids, or palm kernel oil acids to form polyesters which are then epoxidized with peracetic acid or hydrogen peroxide and formic acid.  Other suitable dihydric alcohols include butane-, pentane-, hexane-, decane-, octadecane- and dodecanediols, 2,2 - dimethylpropane - 1,3 - diol, cyclohexane - 1,3 - diol and p - xylylene glycol. Suitable dicarboxylic acids include saturated aliphatic acids having 4 to 10 carbon atoms and aromatic acid such as the phthalic acids.  Other unsaturated acids include dehydrated castor oil acids and acetyl-ricinoleic acid.  The novel products may be used for plasticizing and stabilizing vinyl polymers including polyvinyl chloride, copolymers of vinyl chloride with, e.g. vinyl acetate and vinylidene chloride, polyvinyl acetate and acrylic ester polymer.  The plasticized polyvinyl chloride pastes may be used for coating fabrics, or for casting and dipping applications.ALSO:The invention comprises epoxidized linear polyesters of saturated aliphatic or aromatic dihydric alcohols, dicarboxylic acids free from non-benzenoid unsaturation and unsaturated fatty acids derived from naturally occurring triglyceride oils, which latter may be used in conjunction with saturated fatty acids or aromatic monocarboxylic acids.  Unsaturated polyesters are prepared from the acids or glycols by conventional methods.  They may be epoxidized by known methods such as oxidation using a peracid, e.g. perbenzoic, perphthalic or peracetic acid or by dehydrohalogenation with alkali of the halohydrin obtained from the unsaturated esters with hypohalous acid. The degree of epoxidation may be varied by variation of the time of contact of the ester with the peracid or the halohydrin with alkali or variation of the quantity of peracid or hypohalous acid used. The products may be used as plasticizers and stabilizers for polymers (see Group IV (a)).  Examples are given in which adipic acid and propylene glycol are heated with (1) and (2) oleic acid; (3) lauric acid and tobacco seed oil acids; (4) linseed oil acids; or (5) palm kernel oil acids to form polyesters which are then epoxidized with peracetic acid; or (4) hydrogen peroxide and formic acid.  Other dihydric alcohols which may be used include butane-, pentane-, hexane-, decane-, octadecane- and dodecane-diols, 2:2-dimethylpropane-1:3-diol, cyclohexane-1:3-diol and p-xylylene glycol.  Suitable dicarboxylic acids include saturated aliphatic acids having four to ten carbon atoms and aromatic acids such as the phthalic acids.  Other unsaturated acids include dehydrated castor oil fatty acids and acetyl ricinoleic acid.